title: Photolabile protection of 1,2- and 1,3-diols with salicylaldehyde derivatives.
abstract: 1,2- and 1,3-diols, including carbohydrates, can be readily caged as acetals of 5-methoxy- or 5-hydroxysalicylaldehydes. Irradiation of these acetals with 300 nm light results in their efficient (Phi = 0.2-0.3) cleavage, regenerating an aldehyde and a glycol in excellent chemical yield. Photoreactive 5-hydroxysalicylaldehyde acetals can be produced by mild in situ reduction of photostable p-quinone precursors.
authors.affiliation: Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA.
authors.forename: Alexey P
authors.initials: AP
authors.lastname: Kostikov
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Popik
mesh_terms: D000080:Acetals / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D010777:Photochemistry
chemical_list: D000080:Acetals; D000438:Alcohols; D000447:Aldehydes; C013243:salicylaldehyde